I went ahead and signed up for a year of iTunes Match. It costs $25 for a year. Here's my experience with it so far...
I have a 1tb external usb drive with all my iTunes stuff organized in a folder. In the folder, I have about 90gb of music. It's fairly well organized and mostly has album art and the files are named properly and the tracks are all in order. But I do have some things that are unknown, or just thrown in there. So I moved all those items out for now. Also my bitrates and file formats are all over the place. Mostly mp3 but also some wma's in there along with wav, flac, and many other audio formats. I think I might even have a few things that are drm locked.
But I went ahead and dragged everything over to iTunes. Then I subscribed to Match. It then began a really long 3 step process. The first step seemed to be determining what I had and either uploading it directly or somehow building a library in my iCloud. Hard to say because it doesn't specifically tell you what it's doing. For example, if I have Metallica "Ride the Lightning" then it seems counter-intuitive to actually upload my album when they already have it there in iTunes. And mine is only ripped at 128kbps whereas they are going to give me 256.
Anyway, so not sure what's going on with that. But then the second step seems to be completing the process and shows you it's progress by displaying how many songs it has left to do. The third step is to take anything it's not familiar with and just directly upload it. So if you had some stray recordings of things or things that aren't even technically music files, then those things get uploaded. For example, I have digital audio of some tapes I made when I was a kid. Those seem to now be sitting in icloud (which is a little weird).
So once this is all done, then you can enable iTunes Match on your phone or pad and all your music shows up in the itunes app. And each song has a cloud icon indicating you can download it.
The next step is going to be to redownload everything. Now that it's all uploaded, technically it can all be downloaded with the higher bitrate. And all of it will be unlocked, properly named (if it wasn't already -- i hope) and all in the same file format (which should be mp3 I believe but not 100% sure yet).
It seems that I have roughly less than 8000 songs. This process will handle up to 20,000 songs. I started this whole thing at around 6pm last night and it was almost complete with everything when I woke up this morning. Tonight I will have to restart it and let it finish uploading the straggler songs.
So just wanted to write about this in case anyone else was toying with the idea of trying this. Seems to be going pretty well so far. I'm not sure if this is the answer people want but it's definitely a good way to do this that doesn't require very much (if any) technical knowledge. In other words, it's time consuming but very easy.
